Let the Dream Die: Jon Lester is Gone and He's Not Coming Back

About the Author

Eric Wilbur is a Boston.com sports columnist who is still in awe of what Dana Kiecker pulled off that one time in Toronto. He lives in the Boston area with his wife and three children. Comments and suggestions for the best Buffalo wing spots are encouraged.

I know what he said, but let’s make this clear; Lester won’t go to the highest bidder this winter the same way Roger Clemens went closer to Texas by way of Canada. As Yahoo’s Jeff Passan pointed out, the A’s lefty (now 3-0 with Oakland) is having the best walk year in a generation, with every start bringing him one step closer to a $150 million payday.

“The Los Angeles Dodgers lavished $147 million on Zack Greinke after a season in which he put up a 3.48 ERA. Lester's is nearly a run lower,” Passan notes. “The Phillies gave Cliff Lee a $24 million-a-year deal when his Fielding Independent Pitching – a metric that predicts future performance as well as any using strikeouts, walks and home runs allowed – led the league. Lester's this year is even better. His ERA and FIP top CC Sabathia's in the wake of his remarkable stretch run with Milwaukee in 2008, destroy those of Barry Zito before his $126 million contract and best all the second-tier pitchers who got paid: Anibal Sanchez and John Lackey and A.J. Burnett and C.J. Wilson. Even the pitcher expected to fetch more in free agency than Lester, Detroit ace and reigning Cy Young winner Max Scherzer, trails Lester in ERA and FIP.”

The easy translation is that Lester (13-7, 2.51 ERA) is going to get paid, big time, in the offseason with the Yankees as the obvious front-runner, followed by perhaps the Tigers should they feel Lester is an upgrade over Scherzer, or if they lose their righty in free agency before Lester makes a decision.

Angels? Mariners? Cubs? All could be possibilities. But he’s probably going to New York, an inevitability that Red Sox fans should prepare for in lieu of believing the sunshine, lollipop dream that Lester would return to Boston.

Lester is saying all the right things, leaving the door open to come back to the Red Sox, but then again, what else is he going to say? Give me all the monies?

"[The Red Sox] told me, ‘We’re going to be aggressive. You’re going to get blown out of the water by some of these [other] offers,'” Lester told the Boston Herald’s John Tomase regarding his last conversation with Red Sox owner John Henry. “I’m like, ‘I don’t need to be blown out of the water.’ Why would I need to be blown out of the water? That doesn’t make or break your decision, at least for me. I’m not going to the highest bidder. I’m going to the place that makes me and my family happy. If that’s Boston, it’s Boston."

It’s not going to be Boston.

The last offer the Red Sox made to Lester was the much-ballyhooed four-year, $70 million proposal in spring training. Lester gambled and said “no thanks” to a deal that would have been similar to the club-friendly deal that St. Louis ace Adam Wainwright agreed to with the Cardinals last year, albeit with one fewer year and $27.5 million short. Indeed, five years, $100 million seemed a workable starting point, with Lester’s camp perhaps working its way up to $110 million if the Red Sox refused to add a sixth season to any deal. But after the season that Lester is having, the Sox aren’t even in a similar stratosphere with their original offer, less than half the amount of money the lefty is expected to fetch in free agency. If he leads the A’s to a World Series title with another outstanding postseason to add to his resume, who knows what offers might be presented to his camp?

Lester told Tomase there’s no difference between $150 million and $170 million as long as you’re in a place where you feel comfortable. Maybe that mention of $170 million wasn’t just a flippant number that Lester proposed. It might be a damned near likely scenario.

Oh, it’s fun to imagine a conspiracy theory where the Red Sox and Lester came up with a scheme to get the A’s to surrender slugger Yoenis Cespedes only to have Lester come back to Boston with the offensive firepower he was lacking behind him in place for another run in 2015 and beyond. But isn’t it clear that if the Red Sox are going to fork over $150 million, it’s going to be for an everyday player? After all, it’s not hard to note that while Lester is 3-0 for the A’s, Cespedes is essentially 2-0 for the Red Sox this week alone, with a pair of late-inning home runs over the last two games that led Boston to wins over the Angels and Reds. Cespedes will be back in the lineup Wednesday. Lester won’t pitch again until Sunday.

That doesn’t deny the importance of having an ace in your rotation, but an admission that the franchise seems to not want to invest in having one, taking its chances with its young crop of arms, a lesser free agent veteran, and whatever they can patch together from Clay Buchholz’s shattered promises. If the Sox wanted Lester so badly, they could have made him another offer some time before Ben Cherington told Billy Beane it was a done deal. There was no last-gasp effort. Hell, there was little more than feigned recognition for the guy, despite the season he was having one year after dominating another run to the World Series.

Face it, Lester isn’t part of the future of baseball in Boston. Someone like Giancarlo Stanton, once the Marlins decide to put him on the trade market, is more likely to see an otherworldly contract here, particularly for a team that will eventually be without David Ortiz someday soon. The Red Sox may indeed make a run at Lester, but nobody leaves $20 million or more on the table, despite what he might say in August.

"I want to be happy,” Lester told Tomase. “I want my family to be happy. I want to be comfortable. If that means taking less money, it means taking less money. If it means going to the highest bidder, it means going to the highest bidder, but that’s not going to dictate where I’ll be happy."

Lester is smart enough to do the research (Hello, Carl Crawford), but even he knows which teams will be able – or want - to afford him. The Red Sox can, but they’ve already shown that they won’t. They could still be negotiating with the guy now if they kept him around. Clearly, that wasn’t their priority.

The Red Sox aren’t going to give $150 million to any starting pitcher, whether his name is Jon Lester or not. He’s gone, and he’s not coming back.